


I Dare You!

by Megamonster



Series: Drunk Wincest [3]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Barebacking, Bets, Bottom Dean, Drunk Sex, Drunk Winchester's, Established Dean Winchester/Sam Winchester, Humor, Jealous Dean, Just a glass bottle though, M/M, Marking, Nipple Licking, Object Insertion, Only Dares, Possessive Dean, Riding, Season/Series 06, Smut, Teasing, Top Sam, Truth or Dare
Language: English
Status: Completed
Published: 2018-02-10
Updated: 2018-02-10
Packaged: 2019-03-16 10:59:04
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,614
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13634913
Author URL: https://archiveofourown.org/users/Megamonster/pseuds/Megamonster
Summary: Sometime after Sam gets his soul back, him and Dean go and get drunk; all the while planning on rekindling their relationship. Dean wants to play Truth or Dare just like the first time, Sam, of course, again is a bit hesitant.





	I Dare You!

**Author's Note:**

> Ok, I had technically finished the Drunk Wincest fics, but hey! Another one happened to pop into my brain and just had to write and post it! So I hope you enjoy more drunk Winchester's! ~Meg

Dean pushes Sam through the door and kicks it shut. Slamming his mouth onto his brother’s desperately. Hands grabbing anywhere they could reach, tearing off each layer of shirt they’re wearing.

“Mmm.” Dean mumbled against Sam’s lips as if to say something. Sam finally released his lips and looked down at his brother.

“What is it Dean? We finally get to be alone again in what feels like a long time, don’t ruin the moment by talking.” Sam slurs and purses his lips, diving back in for another sloppy kiss. Dean pushes him off him again to get out what he wanted to say before his drunk mind forgets in about 2 seconds.

“All I wanted to say was that I have an idea.” Sam knits his brows together, boring his glossy eyes into the green meadow like iris’.

“What idea could be more important than getting laid?”

“Do you remember that first night we did, this?”

“Yea.” Sam shifts his stance, swaying slightly.

“What if we did something like that again?” Dean asks wiggling his brows.

“Well, duh. That’s what I planned on doing.” Sam chuckles and boops Dean’s nose.

“You planned truth or dare like I did?” Dean looks confused.

“No, not that. The sex, baby.” Sam connects their foreheads. “I feel like I’ve been gone for centuries, when Cas told me what soulless me did, it made a lot of sense. Everything changed around me, but you, let’s just share this moment without anything as silly as a game.”

“But Sammy, it’ll be fun! Just like the very first time.” Dean places a hand over Sam’s crotch, palming him with the lightest touch. Sam begins panting and bites his bottom lip. He leans back in, locking their lips for a quick kiss.

“Fine. Just as long as the both of us climax tonight.”

“Oh we definitely will.” Dean winks at his brother. “And this is going to be a special kind of truth or dare. We are going to use dares to tease each other, only dares, no truths. So you can’t be a giant pussy about this. And whoever loses, gets to bottom.”

“If you want to bottom Dean, just tell me. Because if I remember, you said you didn’t want to bottom anymore after your first time with me.”

“I don’t want to, figured I’d challenge this because I want another reason to one up you.” He grins.

“But if we are only doing dares, and we have to do them, how are we going to know who loses?” Sam asks.

“Hmm, good point.” Dean taps a finger over his lips to think. “Maybe, whoever can’t take whatever the dare-er dares, loses? Like, if in the middle of the dare the dared is doing, they just can’t hold back, they’d lose.”

“Sounds good, bring it on, dear ol’ brother o’ mine!” Dean walks over to the fridge and grabs the six pack of beers they brought with them. Looping a finger through a belt loop on Sam’s pants and dragging him over to the beds. Shoving him down on one so he sits, and plops down on the one across from him. Things were heating up in the room already, and they’ve barely done anything other than take off their shirts.

Dean hands Sam a beer from the carrier and twists the cap off his own. Downing half of it in two swallows. He sets the bottle down on the end table and waits for Sam to do the same as he drinks his beer straight down. Sighing after dropping the empty bottle to the floor, and burps awfully loud which signaled a giggle out of the happy drunk.

“We aren’t even going to follow the normal rules of truth or dare, just say whatever you can think of.”

“Alright?” Sam quirks a brow and waits for his brother to do something to him. “That’s not even truth or dare then.” He just stares at him with this smirk on his face. Dean scoots forward and traces his thumb over Sam’s shiny lips.

“I’m cumming.” He whispers. Upturning his brows, pulling Sam’s bottom lip down. “I’m cumming.” He whines. “I’m cumming.” Sam darts out his tongue to swipe over the tip of his thumb. Dean slides the digit in his mouth, allowing Sam to suck on it. Feeling his tongue swipe over the pad makes him whimper genuinely. “I’m cumming.” Quietly and panting. He slowly drags his thumb out, pulling on Sam’s bottom lip again, and popping his own thumb in his mouth. Moaning as he cleans his thumb of Sam’s taste. “I’m cumming.” He says around the digit.

“Game on. Doesn’t help that I’m completely smashed right now.” Sam clears his throat. “I feel like we should play by the normal rules, though.”

“Ugh, fine, but my first one still counts as a turn.”

“Whatever.”

“Hmmm, I dare you, to, beg me to make out with you in anyway you can for 2 minutes. But, I have to refuse.” Sam smirks at that.

“Dean will you lock your plush, voluptuous lips with mine?” The eldest shakes his head. “Please?” With the most innocence in his voice, and even in his drunken stupor he was able to pull off his signature puppy dog eyes. Quivering his bottom lip. Dean had to chew the inside of his cheek and look away from Sam.

“No Sammy.” Blushing brightly.

“But Dean, I wanna feel your lips on mine.” Sam crawls off the bed and kneels in front of him. “Your lips are so soft and warm against mine. They’re so tempting, desirable.” He cups Dean’s face and leans in. Sam was so close but Dean pushed him an arms length away.

“No.” He looks into Sam’s eyes this time. Puppy eyes never leaving.

“C’mon Dean.” He begs. “I know you wanna.” Dean makes a quick glance at the clock, can’t contain his grin.

“Times up my sexy puppy.” But Sam’s face never changes. “Alright, a quick kiss.” He pulls him back in for a quick peck. “Your turn. Lay it on me.” Sam grins and sits back on the bed.

“Hmm, I dare you to tease me for one whole minute.”

“Oh baby, I’ll only need a minute.” Dean winks. He lunges off the bed, rushing into Sam as he knocked him down on his back. Dean kisses Sam’s face, peppering lightly over his skin. Holding and turning his head to lick behind his ear. Teasing that little sensitive spot with his tongue and trailing down his neck. Every tingle and hairs that stood up sent a feeling, straight to his cock straining in his jeans.

“Ah fuck.” Sam gasps and places his hands on Dean’s shoulders. Dean nips at the side of his neck and kisses his way back to his ear, biting the lobe; eliciting a moan from the young hunter’s drunken mouth. Sam peels his eyes open to check the time. “Dean, it’s been well over a minute.” But the eldest doesn’t listen, determined to make his little brother lose the game.

Sam sighs as he feels his brother’s tongue drag along his jaw, down and over his adam’s apple into the hollow of his collar bone. Dean leans back with a shit eating grin on his face, “Mmm that was a lot of fun. I'm a little jealous.” He reaches over for his beer and finishes it off, throwing the bottle with the one Sam threw to the floor. Dean grabs another beer for Sam, offering it to him, but Sam refused. Dean shrugged and twisted the cap off that one.

“Why would you be jealous?” Sam pants.

“Not me, my body.”

“Awe, would Deanie Weanie like me to tease him as well?”

“How ‘bout you don’t call me that, ever. And I dare you to tease my nipples with your mouth.” Dean goes to stand, Sam sits up and grabs him by his belt loops. Sam tightens his legs together and guides Dean to sit on his lap, straddling the long, branch like limbs. Sam kisses the top of his stomach, nipping at the flesh with his teeth. “Jesus Sammy.” Dean sighs. “Hold on a minute.” He stretches to the left to set his beer down.

At that moment Sam latches his mouth onto a nipple and laps the growing bud. Dean visibly shudders and laces his fingers in his brother’s hair. Sam sloppily covers the pointed rosey bud in his saliva and pulls away, blowing on it with cool air. Sam moves over to the other one to give it the same treatment. He uses his hand to thumb over the wet bud. He hears Dean whimpering above him, which only eggs him on. Dean grunts and scrapes his nails across Sam’s scalp when he feels teeth nip at his nipple. Twisting and slightly pulling, and bringing out noises that Dean never knew he could make.

Sam pulls off with a wet pop and stared up at his brother’s deep red face, his chest rising and falling with every pant.

“How’s your body feeling now?” He keeps eye contact with him as he kisses his brother’s stomach. Biting down to make a mark, soothing it with a slow swipe of his tongue.

“About this close to just giving up and let you top, but my pride won’t let me do that.” Dean holds up his hand with a tiny separation between his thumb and index finger. “Damn, you sure know how to make me crumble.”

“What can I say, I’ve had years of practice.” Sam smirks up at him.

“Alright baby boy, your turn.” Sam’s eyes darken over more with lust, if possible, at the nickname. “What would you like me to do?”

“I dare you, with your eyes closed and outstretched arms to walk towards me, and kiss the first place you touch.” Dean grins and gets off of Sam. Both of their jeans evidently bulging in the crotch. He holds out his hand, helping him to stand. He leads him to the front of the beds and stands 2 feet in front of him. “Dean, back up some more.” Sam sways and stifles his onslaught of laughter when Dean nearly fell back on his ass. “Close your eyes, hold out your hands and start walking.”

Dean sighs, closing his lids raising his arms out front and he squats. Sam this time couldn’t hide his laughter as Dean started waddling over to him. He couldn’t keep still as his laughter just continued to bubble out of him. He stopped and opened his eyes when he felt something touch his jean cald hard on. Looking down, Dean had run into his crotch with his nose, he watches as his lips dragged from the bottom all the way to where the tip of his dick would be, and kissed there open mouthed. Tongue swiping harshly, wetting the material.

“Fu-uck.” Sam shuddered. “Squatting was your only way to be crotch level, huh.”

“You know it.” He mumbled over his dick. Sam pushed Dean’s head back and forced him to stand. “Oh god, I really can’t wait to fuck you.” Dean says seductively and wraps his arms around Sam.

“ _ I _ can’t wait to fuck you.” Sam repeats resting his forehead on Dean’s.

“Oh no.” Dean slaps his hands on Sam’s ass, grabbing the flesh tightly. “This ass will be mine tonight.” Sam groaned when Dean squeezed his cheeks, pushing against his palms, silently asking for more.

“Then make me lose, big brother.” Dean pushes away from Sam, not waiting for a dare to fall from his lips. He strips out of the bits of clothing and sits back on his bed. Supporting himself on his left elbow as he snakes his hand down his torso to his aching cock. Sam watches in amazement never moving from his spot. Dean moans as he strokes his red cock. It feels hot under his hand, throbbing terribly fast as he touches himself.

“Oh fuck! Wish this was your hand touching me _ unghh _ !” He runs his thumb over the slit as more pre-cum drools out. Dean continues to groan and grunt as he strokes his cock leisurely, tightening his grip on the upstroke. Whimpering exaggeratedly since he knows his brother is watching and listening intently. “ _ Sammy _ !” His eyebrows were upturned and eyes pleading.

Sam goes to take a step and move over to help his brother, but stops, knowing that’s exactly what Dean wants him to do. Dean stops touching himself at Sam’s hesitation. Panting as he collects himself, sitting up on the bed.

“Alright, the game is fucking on.” Sam grits and walks over to the nightstand between the beds, grabbing the bible. Dean knows Sam gets a thrill watching him touch himself, he used to do it when these feelings first protruded back in his prepubescent years. Dean of course had no idea. He thought of a few verses that works against what they do with each other. He went on his hunt, leafing through the pages until he found one of the chapters, Matthew. Scanning through he found the verse. He clears his throat and in the most seductive voice he could muster, he read, “And if your right hand causes you to sin, cut it off and throw it away. For it is better that you lose one of your members than that your whole body go into hell.” Biting his bottom lip as he looks up at Dean. Remembering the other verse, he quickly ran the pages by until he found Romans, “Rather, clothe yourselves with the lord jesus christ, and do not think about how to gratify the desires of the flesh.” He groans at the end. But also mentally slapping himself for even trying to make the word of God sound sexy. His mind really was corrupted if he was thinking that these bible verses would turn his brother on. ‘Well, I’m already going back to hell.’ He thought as he watched Dean cock a brow and make a disgusted face at him.

“What, *sigh* what in the actual fuck were you trying to do?” He asks.

“S-seductively read out of a random book, this was the only book that I knew was in here.”

“Well, it didn’t work, even what we are doing together was less sinful than what you just did.”

“Fine, fuck it, whatever, I forfeit this turn.” He crosses his arms, then reaching down for a beer and twisting the cap off and drinking half of it. ‘I’m sorry God.’ Sam apologized in his head.

“Nah, I’ll let it slide.” Dean smiles to get his brother back on the same page. “Or unless you have something else in mind.” He winks at his brother. Sam smirks and gets his phone out, getting up and walking to the front of the beds. He doesn’t dial in any numbers but pretends to call someone. Sam knows Dean can be possessive, and jealous, this would totally make Sam win if it pushes Dean to that point of growling ‘Mine!’ into Sam’s ear.

“Hey, Cas.” Dean quirks his head to the side and tries to stand up. But Sam snaps his fingers, signalling for him to sit back down on the bed. To which he complied. “So Dean’s out somewhere and I’ve had a  _ few _ too much to drink.” He slurs a little more into the speaker for emphasis. “And I decided to call you and tell you that, I want your angel dick.” He drops his voice an octave. “Mmmm, I’ve imagined you in my dreams so many times that I just can’t take not being able to have it.” Sam watches as Dean’s eyes turn this bright green and his nose bunches on the bridge as the jealousy begins to boil in his veins. “Just me having my lips around that length, you feeling my wet, warm and enveloping mouth sucking you all the way down into my throat. Oh god, Cas, thinking about it is making me so fucking hot!” Sam palms himself over his pants and keeps his eyes on Dean, he’s about ready to attack, just need that final push. “I need you to fuck me, fuck my ass into oblivion, so hard that my asshole leaves an imprint of your dick.” Sam whines as he grips his dick, moaning as he tries to stroke down his cock. His eyes had slipped closed on the last “confession” and didn’t see Dean lift off the bed until he felt his hand tear the phone out of his hand and throw it somewhere in the room and toss him down on the bed. Straddling his hips and pinning his wrists down on the mattress.

“No!” Dean growls with bared teeth. “You are mine! Nobody else’s!” He claims Sam’s mouth in a heated kiss, predatory. Sam doesn’t intend to push Dean off, loving that he was able to make Dean lose, so he let it play out until Dean cooled off a bit. Dean eventually left his brother’s mouth and went straight to his neck, sucking a rather dark mark, eliciting a loud moan out of the giant.

“Fuck, De! Yes, only yours!” Sam gasps as Dean marks up another spot on his neck. “You probably owe me a new phone though.”

“Not my fault.” He says on Sam’s neck.

“Yea it is.” Sam pants.

“You were the one that decided to play dirty and call Cas.”

“I did no such thing.” Sam says, really taking in that Dean sounded, not jealous, pissed. Genuinely pissed. “Go look at my phone.” Dean stares at him hard before pushing off of him to hunt for the phone. Finding it sticking out from one of their duffels, no cracks and works just fine. Dean looks into his recent call history and found no recent calls to Castiel.

“You did that, to get a rise out of me? Use my jealousy and possessiveness against me. You really were playing dirty Sammy.”

“I did it to make you lose.” Sam sits up on the bed.

“That’s cheating.” Dean says walking back over to his brother.

“No it’s not, it was something that came into my mind, I didn’t think you’d get so worked up about a fake phone call to our best friend.”

“So, those confessions were fake?” Dean asks standing in front of Sam.

“Yes.” Sam says loudly.

“So, you have absolutely no interest in our winged halo?”

“Yes.” Sam reiterates. “No interest for anyone but you.”

“Good.” Dean instantly threads his fingers through Sam’s hair and pulls his head back so he stares up further. Sam’s reaction was just as fast, he moans and places his hands over Dean’s hips. “Even though you technically cheated, I don’t really care, I just want to have a fucking orgasm.” He leans down to claim Sam’s mouth again. “ Just make sure I’m properly prepped for that monster in your pants.” He says over his lips. Dean releases his hand and lays down on his back on the other bed.

Sam opens the nightstand drawer again to grab the lube. “This should be a little easier since you’ve taken my dick once before.”

“But it has been a while and I don’t want to be feeling your dick imprint 2 weeks later. Like last time.” Dean says seriously. Sam chuckles and coats 2 of his fingers with the lube. He tosses the bottle by Dean’s legs and reaches for his beer on the nightstand, finishing it off and slinging it to clutter with the others on the floor. He burps and giggles a little. But then Sam happens to look back to the strewn about bottles on the floor, he grins wide as he bends down to grab the closest one to the bed. Placing it back on the table, for later. Dean looks at him kind of weirdly, but his expression changes when Sam teasingly rubs a lube covered finger over his pucker. Making it shine in the lamp lit room.

Sam slowly inserts the the tip of his finger into Dean’s tight heat, pulling it back out as Dean whimpers. On the push back in, Sam shoves his digit all the way inside, immediately curling it up into Dean’s prostate. Which made the eldest spasm, arching his back as choked out moans left his throat.

“You make the most delicious sounds, De.” Sam slurs a bit more.

“Sh-sh-shut uh- _ aagh _ -up!” Sam pulls back from torturing his brother to add in another finger, on the pull out he separates the digits and gains a little speed. Sloppily but yet efficiently opening his brother. When Dean feels good and loose for another, he inches his ring finger in the others. Dean seems to be getting a bit impatient, and quickly fingers him open.

Sam looked up at his brother, whose eyes were closed, panting and moaning while Sam works. He reaches over for the empty beer bottle bracing it between his thighs, lubing up the neck. And without missing a beat, removes his fingers and inserts the bottle into Dean’s clenching hole. Dean’s eyes shoot wide when he feels the glass object enter him. Throwing his head back as a deep grunt rumbled from his chest. The ridges of the lip of the bottle juicily pressing up into his pleasure button. Stars were being shown behind his eyelids the more the bottle sits in that one spot.

“Oh fuck oh fuck oh fuck! You are one dirty mother fucker!” Dean moans loudly when Sam jerks the bottle slightly.

“You know it.” Sam looms over Dean and plants his lips over his neck, peppering dark marks over his skin. Holding onto the bottom rim of the glass, pulling it out and shoving it back in, at a upward angle. Feeling Dean gasp harshly while he attacks his neck is driving Sam mad. “How does this bottle dildo feel in your tight little ass of yours?”

“Feels fucking good.” Dean groans as Sam’s hand moves the makeshift dildo in and out faster.

“Yea?” Sam wolfishly grins when he moves his face away to look at Dean’s. “Would my monster cock feel any better in here?” Sultry dripping from his words as he says them over Dean’s agaped mouth. Dean whines high pitched, opening his eyes to reveal the pleading behind the lust. “So, you want my cock shoved up your tight, wet, asshole? Rubbing in all the right places?” He stops moving his hand to the press the lip of the bottle into Dean’s prostate again. Dean screams as his whole body feels like it’s being electrocuted.

“Please oh please!!” Dean begs. “Fuck me!” A continuous set of pounds are heard on the wall behind the headboard, but neither of them stop to give courtesy to the other guests staying in this motel. They’ll be gone by the morning anyway.

Sam carefully pulled the bottle out of Dean and inserted his three fingers back in, working in his pinky, and pushing in to the second widest part of his hand. Quickly finishing to prep him, he can’t hold back anymore. He pulls his hand back and in a split second stands up and strips out of his bottoms. Picking up the lube again, he slicks up his cock. Dean watches Sam get himself ready, kneeling between his open legs. He wraps his around Sam’s waist, flipping them completely so Dean’s on top. Sam, head spinning after being thrown down by his brother and the alcohol messing with his equilibrium, takes a minute to figure out what happened. He never quite figures it out because he feels something warm beginning to encase his throbbing erection. They both moan, Dean’s thighs slowly trembling and quaking as he feels his asshole surprisingly take in Sam’s girth.

“Oh my god, Sam!” Dean growls and scratches his nails across Sam’s nipples. Grinding himself over Sam’s hips, his cock moving slightly inside him. Sam grabs onto his hips tightly, gripping a bit too tight, but Dean doesn’t mind. He thrusts up, making Dean gasp as he feels his cock move deeper, brushing right up on his sensitive prostate.

“Fuck Dean!” Sam throws his head back when Dean lifts off and slams back down, the headboard slamming into the wall with each force of the bounces. Dean was close as it was, the fucking beer bottle set him so close to orgasm, that he feels like a ticking time bomb. Sam starts meeting him halfway, chasing his own fire. “Oh fuckin’ christ! M’close!” Sam grunts.

“M-me too. Hold out?  _ Fuck! _ ” Sam must be pushing right up on that pleasure spot.

“Try’ta.” Sam pants removing a hand and pulling Dean down into a heated kiss mixed with teeth and sweat. He does try to will his body to hold back, but the way that a warmth spreads across his groin, tells him that he’ll be finishing before Dean does. Soon, though, Dean quickened his pace, bouncing fervently, chasing his orgasm that needs that final push.

“Sam!” He whines pleadingly, Sam knows what he needs. He wraps a hand around Dean’s cock, stripping it at the same pace at his thrusts. Sam holds back just enough to watch his brother lean back, hands clinging onto his knees, mouth open as wide as it can go; and yell out profanities as a glorious feeling ripped through his entire being. Cumming, rope after rope over Sam’s hand onto his chest and stomach.

The youngest kept thrusting up into Dean’s clenching, tight heat. Dean, the champ that he is, helps to get his brother off. He sits fully onto Sam, signalling him to stop. Sam whines exaggeratedly and Dean gets off and kneels on the floor. Licking the lube off of his red aching cock. Sucking the head between his lips and sinking down until his gag reflex protests against the action. He told it to shut the fuck up and take it. Slowly inching Sam’s monster further into his throat, nearly suffocating him in the process.

Once he was buried deep into his wet, convulsing throat, Sam wound his hands into the blonde spikes, panting harshly as he’s holding on by a thread. The warmth never leaving his groin as his toes curl on the floor. Dean chokes and gags around the member, but keeps Sam down. Dean pulls up a little to get some much needed air into his lungs and sinking back down.

“ _ Aagnhh! _ ” Sam tightens his fingers around the strands and can’t help the buck of his hips. Dean sneaks a finger down between Sam’s cheeks, toying around his rim and Sam grips him closer to his groin. “Oh fuck!  _ Deeaann! _ ” Sam shouts as he shoots down his brother’s throat. Tensing and relaxing as his hips jerk every so often. The feeling overwhelming and lets go of Dean’s hair. Dropping his hands down on the bed. He pops off of Sam’s softening cock and coughs, landing on his hands to the side. Labored breathing as he nearly blacked out from choking himself on his brother’s cock.

“Fucking shit man.” Dean rasps and swallows. Looking back to the nightstand, his beer still sitting there. He picked it up and drank the rest to somehow soothe his aching throat. When he finished, throwing the bottle to the floor with a clank, he heard snoring from somewhere. He got up on shaky legs to see his giant of a little brother, fast asleep. Dean grins down at him and shifts him so he’s laying lengthways on the bed. Going into the bathroom and cleaning off his stomach with a wet washcloth, eventually laying down next to him. “Glad to have you back, Sammy.”

**Author's Note:**

> It's the end of the fic if you're reading this, I don't know why I chose the Bible for a dare, I do apologize for using that particular book for something dirty. I feel dirty, but that's ok.


End file.
